- Synthesis and antiviral activity of C-5 substituted β-D- and β-l-D4T analogues
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A series of β-D-2',3'-didehydro-2',3'-dideoxy-nucleosides bearing a tether attached at the C-5 position and their β-L-counterparts was synthesized. Their inhibitory activities against human immunodeficiency vires (HIV) were investigated and compared to establish relationship(s) between compound structure and their antiviral activity. No significant activity was observed for β-D- and β-L-modified nucleosides respectively 7a-c and 14a-c, but 7d and 14d exhibited a weak activity against HIV-1.
- Delbederi,Fossey,Fontaine,Benzaria,Gavriliu,Ciurea,Lelong,Laduree,Aubertin,Kirn
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- 1H, 13C and 15N NMR Studies of 13C and 15N Labeled 2-Methylthiooxazoline Derivatives of Pentoses and Hexoses. Stereoelectronic Effects on Chemical Shifts and Mass Fragmentation Pathways
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A facile synthesis of 2-methylthio-(glyco)oxazoline derivatives has been developed which involves methylation of 2-thiono-(glyco)oxazolidines prepared by condensation of aldoses with thiocyanate ion.The synthesis has been applied to the preparation of six 2-methylthiooxazoline derivatives in the pentose series and six derivatives in the hexose series.For several sugars, both pyranoid and furanoid forms were isolated, and the use of either 13C- or 15N-labeled thiocyanates yielded either 2-13C-labeled or 3-15N-labeled derivatives.The structures of the products have been studied by 1H, 13C and 15N NMR spectroscopy and by electron-impact and field desorption mass spectrometry.Multinuclear chemical shift correlations and analyses of fragmentation pathways have facilitated the assignment of ring size in the 2-methylthio-(glyco)oxazoline derivatives.KEY WORDS 1H NMR, 13C NMR, 15N NMR, 2-methylthio-(glyco)oxazolines, ring size
- Davidson, Robert M.,Byrd, Gary D.,White, Edward,Margolis, Sam A.,Coxon, Bruce
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- SYNTHESIS OF NITROGEN-15-LABELED 2-AMINO(GLYCOFURANO)OXAZOLINES via GLYCSYLAMINE INTERMEDIATES
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A new, efficient synthesis of doubly (15)N-labeled 2-amino-oxazoline derivatives of pentoses and hexoses has been delineated that involves treatment either of unprotected or O-isopropylidenated glycosylamines with cyanamide-(15)N2 in methanol to give 2-amino(glycofurano)oxazolines-(15)N2.A probable mechanism for these reactions is presented.These techniques provide a practical means by which a variety of stable or radioactive isotopes can be introduced into any of several known, clinically significant pyrimidine anhydronucleosides, such as 2,2'-anhydro-(1-β-D-arabinofuranosylcytosine)(cyclo-C).
- Davidson, Robert M.,White V, Edward,Margolis, Sam A.,Coxon, Bruce
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- Pseudo-dumbbell-type molecular beacon probes bearing modified deoxyuridine derivatives and a silylated pyrene as a fluorophore
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We have recently reported a novel pseudo-dumbbell-type molecular beacon probe (Probe 1) possessing polyamine-connected deoxyuridine (U) and silylated pyrene. The probe showed weak fluorescence signal while it stayed alone. Fluorescence signal of the probe was increased in the presence of the complementary DNA. In this study, we prepared new molecular beacons, Probe 2 and Probe 3, possessing the elongated stem portion of Probe 1. In addition, one U in Probe 2 is substituted by anthraquinone-bearing deoxyuridine residue (Y) in Probe 3. Probe 4 is essentially the same as Probe 1 but one deoxyguanosine in the loop portion of Probe 1 is substituted by deoxyinosine in Probe 4. In Probe 5, 3′- terminal deoxycytidine of Probe 3 is substituted by deoxyadenosine. The fluorescence signal of these probes is effectively quenched in the absence of target DNA. Among all, Probe 3 shows the most effective quenching. On the other hand, the signal is substantially increased in the presence of complementary DNA. The ratio of signal to background in case of Probe 3 is the highest. All these probes also recognize single nucleotide alternation in the target DNA to a different extent. The sequence recognition ability of Probe 3 is also the highest among all the probes.
- Chowdhury, Jakir Ahmed,Moriguchi, Tomohisa,Shinozuka, Kazuo
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supporting information
p. 496 - 502
(2015/03/31)
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- Phosphate-mediated interconversion of Ribo- and Arabino-configured prebiotic nucleotide intermediates
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(Represented Chemical Equation) Flipping stereochemistry: Inorganic phosphate catalyzes the interconversion of ribose and arabinose aminooxazolines, suggesting that the prebiotic synthesis of enantiopure pyrimidine ribonucleotides might have involved a single stereoinversion at Cl′ and a double stereoinversion at C2′.
- Powner, Matthew W.,Sutherland, John D.
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supporting information; experimental part
p. 4641 - 4643
(2010/09/07)
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- Synthesis of analogues of 1-(2',3'-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine
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This work describes the synthesis of three new anti-HIV analogues of 1-(2',3'-dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine by two different routes. The compounds were functionalized on the 5-position by a carboalkoxymethyl group. The C-5 substituent on
- Fontaine,Lequenne,Fossey,Renoud-Grappin,Laduree
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- Facile Synthesis of 5-Substituted Arabinofuranosyluracil Derivatives
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Arabinoaminooxazoline reacted readily with α-(bromomethyl)acrylate derivatives to afford the corresponding adduct.Potassium tert-butoxide- or sodium methoxide-catalyzed cyclization of the adduct gave 5-substituted 2,2'-anhydroarabinofuranosyluracil derivatives.
- Sawai, Hiroaki,Hayashi, Hidekazu,Sekiguchi, Sumie
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p. 605 - 606
(2007/10/02)
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